DE2833013A1 - NEW ALUMINUM-SULFUR COMPOUND, METHOD OF MANUFACTURING IT, AND MEANS OF CONTAINING THIS COMPOUND - Google Patents

Description

J. RBITSTÖTTBR W. KINZEBACH

PROF. DR. DR. DIPL. ING. DR. PHIL. DIPL. CHKM.

W. BUNTE (1958-1976) K. P. HÖLLER

DR. INO. DR. RBR. NAT. DIPL. CIIBM.

TBLEFOM: (OSO) 37 GB 83 TELBXl E21620S ISAR D

BAUERSTRASSGi 22. 8000 MONCHBN

July 27, 1978 M / 19 177

L ¹ OREAL

14, rue Royale

F-75008 Paris, France

New aluminum-sulfur compound, process for its preparation and means containing this compound

POSTAL ADDRESS! POST BOX 780, D-SOOO MUNICH 43

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M / 19 177

The invention relates to a new aluminum-sulfur compound, Process for their preparation and cosmetic and pharmaceutical compositions containing this compound.

The applicant already has in its French patent specification No. 72.34794 suggested the use of sulphurous ammonium salts, which have antimicrobial properties have, these compounds mainly in deodorant-antiperspirant agents, Anti-dandruff agents as well as used in personal care products and especially in feminine hygiene will.

The field of application of these compounds, which is a had excellent effectiveness but was limited by their poor solubility in water and alcohol.

, The present invention relates to a new sulfur-containing aluminum salt, which has better solubility and excellent

: shows effectiveness and now the realization

a large number of cosmetic and pharmaceutical agents

erm light.

The present invention relates in particular to aluminum tris (N-oxy-pyridine thiolate) the formula:

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The compound is in the form of a whitish powder; their molecular weight for C ₁₅ H ₁₃ N ₃ O ₃ S ₃ Al = 405.

The compound is extremely effective against gram-positive Bacteria such as Staphylococcus aureus, Bacillus Subtilis and Micrococcus Luteus; gram negative bacteria such as Escherichia

CoIi, Klebsieila Pneumoniae, and Pseudomonas aeruginosa; ι .. ■

against yeasts such as Saccharomyces Cerevisiae and Candida Lipolytica, and against molds such as Aspergilus Niger and Penicillium Notaturn.

The invention also relates to the method for producing Aluminum tris (N-oxy-pyridine thiolate) according to the following Reaction scheme:

CH.

CH.

O - Al I

- 0 - CH

CH

+ 3 HO - CH '

CH ₃

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Aluminum isopropylate (2) is reacted with three molar equivalents of pyridine-N-oxide-2-thiol (1). The reaction takes place in an anhydrous solvent, preferably selected from aromatic hydrocarbons, such as benzene or Toluene, chlorinated solvents such as dichloroethane or chloroform, and alcohols such as isopropanol.

In this process it is not necessary to heat, but moderate heating, generally to between 20 ^° C. and 100 ^° C., can shorten the reaction time.

The active ingredient is then isolated by concentrating the solvent under reduced pressure.

The invention also relates to cosmetic and pharmaceutical agents which contain aluminum tris (N-oxypyridine thiolate) as the active ingredient of formula (I) included.

The active ingredient of the present invention is preferred alone, optionally with a mixture with other active ingredients, especially together with aluminum tri- (camphor-10-sulfonate) used.

It has even been found that by combining
Aluminum tris (N-oxy-pyridine thiolate) with aluminum tri- (camphor-10-sulfonate) can still increase the solubility of the active ingredient according to the invention.

If about 3% aluminum tri- (camphor-10-sulfonate) is added, so you can double the solubility of aluminum tris (N-oxypyridine thiolate).

The active ingredient according to the invention can be used alone or in combination with other active ingredients, especially aluminum tri- (camphor-10-sulfonate), be included in a variety of cosmetic or therapeutic agents, which either for

909807/0860

hygienic purposes or for the treatment of warm-blooded animals (including humans), as well as for topical as are also intended for oral administration. The active according to the invention Active ingredient can be found particularly in deodorants, disinfectants, and antiseptic for personal hygiene Means, means for intimate hygiene, the hygiene of the scalp and in general for the care of the entire body skin and hair; used in anti-dandruff, anti-acne, anti-fungal agents. in the In general, the compound according to the invention can be contained in all agents which are used for prophylaxis or treatment any pathological phenomena in which microorganisms are involved, for example pityriasis, Onyxis, Intertrigo, Dermatomycosis, Dermatophytosis, Impetigo, infected dermatosis, athlete's foot, pruritus of infectious origin, Hyperhidrosis or parasitosis.

The active ingredient according to the invention can also be used as a preservative be used.

Those according to the invention intended for topical application Agents generally contain 0.01 to 10% by weight, preferably 0.05 to 3% by weight, of the active ingredient according to the invention.

These agents intended for topical use can be in various forms, in particular as a liquid shampoo, Dry shampoo, lotion, cream, milk, stick, powder, soap, · gel, ointment or as alcoholic, dry or powder spray.

The creams are preferably "oil-in-water" emulsions represent which to -10 to 50% off oil and ~ 90 to 50% off Water.

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About the oils used for the oil phase of the emulsions include in particular:

Hydrocarbon oils such as paraffin oil, purcellin oil, perhydrosqualene and solutions of microcrystalline wax in oils,

animal or vegetable oils, such as sweet almond oil, avocado oil, calophyllum oil, lanolin, castor oil, horse oil, pork oil and olive oil,

Mineral oils, in which the distillation at atmospheric pressure at eti

ends,

begins at about 250 ⁰ C and in the order of 410 ° C

saturated esters, especially isopropyl palmitate, alkyl myristates, such as isopropyl, butyl and cetyl myristate, Hexadecyl stearate, ethyl palmitate, triglycerides of octanoic acids and decanoic acids and cetylricinoleates.

You can also use silicone oils in the oily phase, which are soluble in other oils, such as dimethylpolysiloxane, Methyl-phenylpolysiloxane and the silicone-glycol polymer.

In order to promote the retention of the oils, the oily phase can also contain waxes, such as carnauba wax, Candelilla wax, beeswax, micro-crystalline wax and ozokerite.

For the production of the creams according to the invention one can also Fatty alcohols, such as stearyl alcohol, cetyl alcohol, 2-octyl-1-dodecanol, oxyethylated fatty alcohols and propylene glycol. use.

If the agents according to the invention are in the form of sticks, so these consist of melted waxes in which in

909807/0860

Form an emulsion an aqueous alcoholic. or aqueous-alcoholic solution or suspension of the active ingredient defined above is added.

; A certain amount of oils or fatty alcohols can also be included in the waxes. In general, one can use for To make the pencils, use the same waxes, oils and fatty alcohols as described above for the creams.

The emulsifying agents for this type of agent can be conventional emulsifying agents, in particular fatty amides, such as coconut fatty acid monoethanolamide, Stearic acid diethanolamide, etc.

The agents according to the invention present in powder form contain Talc or other corresponding substances, as well as a certain amount of fat, so that the powder obtained can agglomerate.

The agents according to the invention can also be in aerosol form; it can be alcoholic sprays, dry or. Powder, be sprays. In this embodiment, the proportion is of active ingredient between 0.01 and 5% by weight, based on the total weight of the aerosol agent. .

In addition to the active ingredient, the alcoholic sprays present in aerosol form contain an anhydrous alcohol such as ethanol or isopropanol and one or more propellants such as fluorochlorinated hydrocarbons, lower hydrocarbons, carbon dioxide, nitrous oxide and / or nitrogen . material. You can also add methylene chloride.

\ The present as a dry spray compositions of the invention | In addition to the active ingredient and the propellant liquefied under pressure, they contain talc or similar substances together with ■ a certain amount of fatty substances such as oils or fatty alcohols. ^;

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The agents according to the invention intended for topical application can of course also other conventional ingredients, such as penetrants, perfumes, dyes or thickeners, contain.

Those according to the invention intended for oral administration Means can be in various forms, in particular as tablets, coated tablets, capsules, pills, powders, granules, Gelcapsules, bolus, drug potion, suspension or solution and preferably contain the active ingredient in an amount between 0.01 and 80%.

Oral administration can either be used for healing or, in smaller doses, for prevention. The single dose of active ingredient can be between 0.001 and 200 mg / kg depending on the type of animal or the person being treated and the nature of the infection.

When the agents according to the invention are in solid form the active ingredient is ground to a fine powder which can be used in a conventional manner for pharmaceutical or pharmaceutical use Mixes diluents used for veterinary purposes. These include starch, lactose, talc, magnesium stearate,, vegetable gums, pectin, dextrin, agar-agar, calcium phosphate, kaolin and / or bentonite.

If desired, one can also use a sweetener, for example Add sugar or an aromatic essence. The tablets or capsules can also be coated in a conventional manner The coating is not soluble in gastric juice but in the intestinal fluid.

If the product is in the form of capsules or gel caps, \

the active ingredient is enclosed in a pharmaceutically acceptable hard or soft gelatine shell. |

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The solutions or suspensions of the active ingredient may be in water, an alcohol, such as ethanol, propylene glycol, glycerol, sorbitol, A ^- be formulated thyldiglycol, butyl diglycol, pyrrolidone, N-alkyl pyrrolidone and / or Ν, Ν-dialkylacetamide.

Vegetable oils such as peanut oil, olive oil, corn oil or sesame oil can be used as liquid diluents.

The drug potions can be in solid form and "must then be dissolved in water before administration, they can also contain surfactants, which favor the formation of a solution or an emulsion.

The active ingredient according to the invention can also be used as a feed additive be used in animal feed.

In this case, the active ingredient is added to food, such as in particular soy, cotton, linseed and / or sunflower press cakes; Corn gluten flour; Corn, wheat, Fish, citrus fruit and / or bone meal; Limestone, ground oyster or egg shells; finest soy flour, soluble molasses extracts, by-products from mills, etc. In this embodiment, the active ingredient is in the Food generally contained in an amount of 1 to 2 ppm by weight. If the active ingredient is diluted beforehand, so the concentration in the premix can be from 0.1 to 20% by weight.

If aluminum-tri- (camphor-10-sulfaont) is mixed with the If the active ingredient according to the invention is used, it makes up between 0.05 and 30%.

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The following examples of the preparation of the invention Connection and the various application examples are intended to explain the invention in more detail without, however, restricting it.

Production of aluminum tris (N-oxypyridine thiolate) (I)

20.4 g (0.1 mol) of aluminum isopropylate are dissolved in 200 ml of dichloroethane and 38.1 g (0.3 mol) of pyridine-N-oxide-2-thiol are then added with stirring. After the exothermic reaction has ended (about 1/4 hour), the mixture is refluxed for 2 hours, then evaporated to dryness under reduced pressure and 40.3 g of the desired active ingredient are obtained in the form of a white powder (theoretical amount: 40.5 g ). Analysis Al calculated: 6.66%
found: 6.70%

Production of aluminum tri- (camphor-10-sulfonate)

3 al

69.6 g (0.3 mol) of camphor-10-sulfonic acid are added with vigorous stirring to a solution of 20.4 g (0.1 mol) of aluminum isopropylate in 200 ml of anhydrous isopropanol. One stirs then continue for about 30 minutes and then reflux the reaction mixture for 90 minutes. The solvent is at concentrated under reduced pressure in a rotary evaporator and the resulting solid is dried in a drying oven at 115 Dried constant weight.

C to

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72 g of a white solid with a crystalline appearance are obtained in this way (theoretically expected amount 72 g).

Analysis: Al calculated: 3.74%
found: 3.70%

Manufacturing examples

example 1

According to the invention, a deodorant lotion is also provided Anti-dandruff and antiseptic effects by mixing the following ingredients:

Aluminum tris (N-oxy-pyridine thiolate) 0.05 g

Aluminum tri- (camphor IO-sulfonate) 0.1 g

Menthol 0.05 g

Ethanol 50 g

make up to 100 g with water

If you wear this product on flaky hair for 15 days daily, one notices a reduction in the dandruff.

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M / 19 177-16-2833Q13

example

According to the invention, a deodorant cream is produced, by mixing the following ingredients:

Cetyl stearyl alcohol, oxyethylated

with 15 moles of ethylene oxide 10g

Cetyl alcohol. 2 g

Whale rat 2 g

Vaseline oil 5 g

Sweet almond oil 1 g

natural rosemary essence 0.2 g

natural lavender essence 0.3 g

Geranium essence 0.1 g

Aluminum tris (N-oxy-pyridine thiolate) 0.15 g

make up to 100 g with water

If you apply this cream regularly, the formation becomes more unpleasant Prevents odors.

example

According to the invention, a deodorant cream is made for the foot care by mixing the following ingredients:

auto-emulsifiable glycerine stearate 6 g

Stearic acid 2 g

Castor oil 2 g

Vaseline oil. 5 g

Isopropyl myristate 3 g

Allantoin 0.3 g

Camphor 0.3 g

Menthol - 0.2 g

Aluminum tris (N-oxy-pyridine thiolate) 0.6 g

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Aluminum tri- (camphor-10-sulfonate) 2.4 g

make up to 100 g with water

example

According to the invention, an emulsion with deodorant and antiseptic effect, which is applied by roller pens by mixing the following ingredients:

Lauryl alcohol, oxyethylated with 2 to 3 mol
Ethylene oxide 0.5 g

Vaseline oil 2.5 g

Lanolin 1g

higher fatty alcohols (50/50 mixture of

Stearyl and cetyl alcohols) 1.5 g

Wheat starch 2g

Aluminum tris (N-oxy-pyridine thiolate) 0.1 g

Aluminum tri- (camphor-10-sulfonate) 0.1 g

make up to 100 g with water

Example 5

According to the invention, a deodorant milk is produced, by mixing the following ingredients:

Magnesium lauryl sulfate 20 g
colloidal silicon dioxide 6g

C ₁₄ to C ₁₈ fatty acid glycerides 5g

Aluminum tris (N-oxy-pyridine thiolate) 0.2 g

microencapsulated perfume 20 g

Milk powder, as much as necessary for 100 g

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M / 19 177-18-2333013

example

According to the invention, a body milk with deodorant and antiseptic effect for dry skin by mixing the following ingredients:

Aluminum tris (N-oxy-pyridine thiolate) 0.5 g

Aluminum tri- (camphor-10-sulfonate) 2 g

Keratin proteolysate 10 g

d-1 Norvaline 0.5 g

aqueous placenta extract 5 g

Sodium Alginate '0.5g

Vaseline oil 5 g

Lanolin 1 g

polyoxyethylated oleic alcohol 5 g

make up to 100 g with water

Example 7

According to the invention, a protective and disinfectant is produced Spray by mixing the following ingredients:

Ethyl p-amino-benzoate 0.5 g

Ethylhexyl adipate 10.3 g Wheat germ oil 1 g

Azulene 0.10 g

Aluminum tris (N-oxy-pyridine thiolate) 0.05 g

Aluminum tri- (camphor-10-sulfonate) 0.1 g

Ethanol 80 g

This mixture is then conditioned together with CO ~ in an aerosol atom, so that there is an internal pressure of 8 bar.

90§8Ö7 / 08SÖ

Example 8

According to the invention, a powder spray for foot care is provided by mixing the following ingredients:

Aluminum tris (N-oxy-pyridine thiolate) 2 g

Titanium oxide 5 g

Kaolin. 5 g

Lavender essence 1 g

fill up with talc (20 μ) to 100 g

10g of this agent is filled into an aerosol container with 54 g of trichlorofluoromethane and 36 g of dichlorodifluoromethane .

example

According to the invention, antiseptic healing talc is prepared by mixing the following ingredients:

Magnesium stearate 5 g

Zinc oxide 5 g

Boric acid 2 g

Undecylenic acid 0.2 g

Aluminum tris (N-oxy-pyridine thiolate) 3 g

fill up with talc to 100 g

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Example 10

According to the invention, a deodorant and antiseptic

^: Manufacture a medium with which to impregnate tissues intended for feminine hygiene by mixing the following ingredients:

^: Aluminum tris (N-oxy-pyridine thiolate) 0.1 g

^: Aluminum tri- (camphor-10-sulfonate) 0.1 g

Ethanol ■ 70 g

any perfume 1 g

ι fill up with water to 100 g

Example 11

According to the invention, an anti-acne milk is produced by the following ingredients are mixed:

Cetyl stearyl alcohol, polyoxyethylated cetyl alcohol

tert-butyl hydroxyanisole Stearic acid

mineral oil

Vegetable oil

Polyoxyethylated derivative isopropyl myristate

any perfume

5-amino-3-thia-hexanedicarboxylic acid aluminum tris (N-oxy-pyridinthiolate)

Aluminum tri- (camphor-10-sulfonate) 3 g

Triethanolamine as much as required for pH 4.2

make up to 100 g with water

2.6 G G 2.6 G G 0.01 G 1.6 G 6.85 G 1.3 G 0.26 G 4.5 G 0.3 G 1 0.7

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Example 12

According to the invention, an anti-acne cream is produced by the following ingredients are mixed:

Cetyl alcohol 7 g

Mineral oil 5 g

Stearic acid 2 g

polyoxyethylated sorbitol derivative 16 g

Allantoin 0.3 g

Azulene 0.1 g

Aluminum tris (N-oxy-pyridine thiolate) 0.7 g

Aluminum tri- (camphor-10-sulfonate) 3 g

make up to 100 g with water

If you apply this cream regularly in the evening, you will see an improvement in the skin and the disappearance of the acne pimples fixed.

Example 13

According to the invention, tablets are made against infections Germs or parasites by mixing the following ingredients:

Lactose, 150 mg

Gum arabic 100 mg

Strength 100 mg

Aluminum tris (N-oxy-pyridine thiolate) 10 mg

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Example 14

According to the invention, a lotion is produced for daily use against dandruff or parasites by mixing the following ingredients:

Aluminum tris (N-oxy-pyridine thiolate) 0.1 g

Aluminum tri- (camphor-10-sulfonate) 0.2 g

Perfume 0.1 g

Dye 0.1 g

Make up to 100 ml with 50% ethyl alcohol

Example 15

According to the invention, an antiseptic cream is produced, by mixing the following ingredients:

Aluminum tris (N-oxy-pyridine thiolate) 0.2 g

Aluminum tri- (camphor-10-sulfonate) 0.2 g

Glycol stearate 1 g

Cetyl alcohol 4 g

Polyoxyethylene stearate to 20 moles of ethylene oxide 6 g

Isopropyl palmitate 10 g

Calophyllum oil 1 g

Perfume at will

with sterile, demineralized water

make up to 100 g

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Example 16

According to the invention, a dermatological stick is made by mixing the following ingredients:

Aluminum tris (N-oxy-pyridine thiolate) 0.1 g

"Igepön A", sodium alkane sulfonate (GAF) 81.5 g

Lantrol, liquid lanolin fraction (Malstrom) 12 g

Perhydrosqualene 2g

Titanium dioxide 2g

Perfume 2.5g

Example 17

According to the invention, an antiseptic skin lotion is produced by mixing the following ingredients:

Aluminum tris (N-oxy-pyridine thiolate) 0.7 g

Aluminum tri- (camphor-10-sulfonate) 2.5 g

^! Ethyl alcohol 13 ml

Polyethylene glycol 10g j Perfume at will

soluble dyes at will

Make up to 100 g with demineralized, sterile water

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Example 18

According to the invention, a liquid anti-dandruff shampoo is produced by mixing the following ingredients:

Lauryl alcohol, polyglycerinized with 4 moles

Glycerin 15 .g

quaternized vinyl pyrrolidone

copolymer (Gafquat 755 from GAF) 0.4 g

Aluminum tris (N-oxy-pyridine thiolate) 0.5 g

Aluminum tri- (camphor-10-sulfonate) 1 g

polyoxyethylated alkylamine, under the

Designation Ethomeen 18/15 distributed

(Rhone Progil) 0.8 g

Lactic acid up to pH 5

Perfume at will

Make up to 100 ml with water

If you apply this shampoo regularly once or twice a week, you can significantly reduce dandruff.

Example 19

According to the invention, granules for chewing are produced against Parisites or microbial infections can help by mixing the following ingredients:

Sucrose 200 g

Lemon syrup 50 g

Aluminum tris (N-oxy-pyridine thiolate) 0.4 g

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Example 20

According to the invention, antiparasitic and antiseptic ones are produced Swallow coated tablets by mixing the following ingredients:

Aluminum tris (N-oxy-pyridine thiolate) 5 mg

Lactose 300 mg

Gum arabic powder 100 mg

simple syrup up to 500 mg

If you administer two of these coated tablets daily, you can treat all types of parasitosis effectively.

B e dks ρ i e 1 21

According to the invention, an antiseptic stick is produced, by mixing the following ingredients:

Sodium isethionate and coconut fatty acid esters R COO CH ₂ CH ₂ SO ₃ Na 74 g

(R = fatty acid derivative with 12 to 18
Carbon atoms)

Lanolin and lecithin derivatives, 23 g

Aluminum tris (N-oxy-pyridine thiolate) 1 g

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Example 22

According to the invention, a powder shampoo against dandruff is provided and parasites by mixing the following ingredients:

Sodium Lauryl Sulphate 50 g

Sodium isethionate and coconut fatty acid esters of the formula R COO CH ₂ CH- SO ₃ Na,

wherein R is C 1 -C ₁₇ radicals 41 g

Aluminum tris (N-oxy-pyridine thiolate) 5 g

Perfume at will 1 g

At the time of application, the powder is dissolved in a 10-fold amount by weight of water.

Example 23

According to the invention, a liquid anti-dandruff shampoo is produced by mixing the following ingredients:

Lauryl alcohol, polyoxyethylated with

12 moles of ethylene oxide 13 g

Coconut fatty acid diethanolamide 4 g

quaternized vinyl pyrrolidone copolymer
(Gafquat 755) 0.4 g

Aluminum tris (N-oxy-pyridine thiolate) 0.3 g

Lactic acid, as much as necessary for pH 5
Perfume at will
Make up to 100 ml with water

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Example 24

According to the invention, a nourishing mask is produced by mixing the following ingredients:

oxyethylated lanolin 5 g

Cetyl alcohol 2 g

auto-emulsifiable ethylene glycol stearate 7 g

Vaseline Codex 5 g Kaolin 10 g

j titanium oxide 8 g

<Aluminum tris (N-oxy-pyridine thiolate) 0.15 g

make up to 100 g with water

Example 25

According to the invention, an anti-mycotic and anti-acne gel is produced by mixing the following ingredients:

Polymethacrylic acid, sold under the trade name Carbopol 940, 1.5 g

Aluminum tris (N-oxy-pyridine thiolate) 0.9 g

Aluminum tri- (camphor-10-sulfonate) 3.2 g

Propylene glycol 5 g

Triethanolamine as much as required for pH 5
make up to 100 g with water

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Claims (18)

Claims : j. Aluminum tris (n-oxy-pyridine thiolate) of the following formula I: S-Al-S 2. Process for the preparation of the compound according to claim 1, characterized in that one is in an anhydrous Solvent aluminum isopropylate is reacted with three molar equivalents of pyridine-N-oxide-2-thiol. Process according to Claim 2, characterized in that the anhydrous solvent used is benzene, toluene, Dichloroethane, chloroform and / or isopropanol are used. A method according to any one of claims 2 or 3, characterized in that the mixture is heated to a temperature between about 20 ° C and 100 ⁰ C. 5. Cosmetic agent, characterized in that it in a suitable cosmetic carrier a sufficient one 90980 7/0860 M / 19 177 Amount of the active ingredient of claim 1, or prepared according to one of the methods of claims 1 to 4 contains. 6. Means according to claim 5, characterized in that the active ingredient in an amount between 0.01 and 10 wt. is preferably comprised between 0.05 and 3% by weight, based on the total weight of the agent. 7. Agent according to one of claims 5 and 6, characterized in that that it is mixed with the active ingredient aluminum tri- (camphor-10-sulfonate) contains. 8. Composition according to claim 7, characterized in that the aluminum tri- (camphor-10-sulfonate) in an amount between 0.05 and 30 wt .-%, based on the total weight of the agent, is included. 9. Agent according to one of claims 5 to 8, characterized in that that it is in the form of a liquid shampoo, a dry shampoo, a lotion, cream, milk, stick, Powder, soap, gel, ointment, or as an alcoholic, dry or powdery spray. 10. Agent according to one of claims 5 to 9, characterized in that that there are also cosmetic ingredients such as penetrants, perfumes, dyes or thickeners contains. 909807/0860 ί μ / 19 177 11. Means for use as a pharmaceutical or in the animal medicine, characterized in that it is in a suitable Carrier a sufficient amount of the active ingredient of claim 1, or obtained by a method of claims 2 to 4. 12, means according to claim 11, characterized in that the active ingredient in an amount between 0.01 and 80 wt. ~ % ■ / based on the total weight of the agent. . 13. Agent according to one of claims 11 and 12, characterized in that that it can be administered in doses of 0.001 to 200 mg / kg. 14. Composition according to one of claims 11 to 13, characterized in that it is mixed with the active ingredient Contains aluminum tri- (camphor-10-sulfonate). 15. Means according to claim 14, characterized in that the aluminum tri- (camphor-10-sulfonate) in an amount between 0.05 and 30 wt .-%, based on the total weight of the agent, is included. 16. Agent according to one of claims 11 to 15, characterized in that that it is in the form of tablets, coated tablets, capsules, pills, powder, granules, gel capsules, bolus, Drug drink, suspension or solution 'is present. 909807/0860 17. Feed, characterized in that it is in one Food carrier as an additive a sufficient amount of active ingredient of claim 1, or obtained according to one The method of any one of claims 2 to 4 included. 18. Feed according to claim 17, characterized in that the active ingredient in an amount by weight between 1 and 2000 ppm. 909807/0860